JP2011516578A5 - - Google Patents
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- JP2011516578A5 JP2011516578A5 JP2011504210A JP2011504210A JP2011516578A5 JP 2011516578 A5 JP2011516578 A5 JP 2011516578A5 JP 2011504210 A JP2011504210 A JP 2011504210A JP 2011504210 A JP2011504210 A JP 2011504210A JP 2011516578 A5 JP2011516578 A5 JP 2011516578A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- aryl
- acid
- cycloalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 229910052757 nitrogen Inorganic materials 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 29
- -1 cycloalkylene radical Chemical class 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 22
- 125000005842 heteroatoms Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000004429 atoms Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000011780 sodium chloride Substances 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 9
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 8
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000002346 iodo group Chemical group I* 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 5
- VAUDXPRANUFYEC-UHFFFAOYSA-N 2-(chloroamino)-5-phosphonopentanoic acid Chemical compound OC(=O)C(NCl)CCCP(O)(O)=O VAUDXPRANUFYEC-UHFFFAOYSA-N 0.000 claims description 4
- COIDHHVBAVTJFV-UHFFFAOYSA-N 2-(dichloroamino)-5-phosphonopentanoic acid Chemical compound OC(=O)C(N(Cl)Cl)CCCP(O)(O)=O COIDHHVBAVTJFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- QUOIXMXPWCACSF-UHFFFAOYSA-N 1-(dichloroamino)propylphosphonic acid Chemical compound CCC(N(Cl)Cl)P(O)(O)=O QUOIXMXPWCACSF-UHFFFAOYSA-N 0.000 claims description 2
- XIGJZYVHLIRSFU-UHFFFAOYSA-N 2-(bromoamino)-5-phosphonopentanoic acid Chemical compound OC(=O)C(NBr)CCCP(O)(O)=O XIGJZYVHLIRSFU-UHFFFAOYSA-N 0.000 claims description 2
- KBINJLBTMJFAPH-UHFFFAOYSA-N 2-(chloroamino)-2-methylpropane-1-sulfonic acid Chemical compound ClNC(C)(C)CS(O)(=O)=O KBINJLBTMJFAPH-UHFFFAOYSA-N 0.000 claims description 2
- SCFWQPHRDQRQIW-UHFFFAOYSA-N 2-(chloroamino)-8-phosphonooctanoic acid Chemical compound OC(=O)C(NCl)CCCCCCP(O)(O)=O SCFWQPHRDQRQIW-UHFFFAOYSA-N 0.000 claims description 2
- NMMHHSLZJLPMEG-UHFFFAOYSA-N 2-(chloroamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNCl NMMHHSLZJLPMEG-UHFFFAOYSA-N 0.000 claims description 2
- LUUQPFYRGJMKIV-UHFFFAOYSA-N 2-(chloroamino)ethylphosphonic acid Chemical compound OP(O)(=O)CCNCl LUUQPFYRGJMKIV-UHFFFAOYSA-N 0.000 claims description 2
- IPWWLXWYFSGQFM-UHFFFAOYSA-N 2-(chloroamino)propane-1-sulfonic acid Chemical compound ClNC(C)CS(O)(=O)=O IPWWLXWYFSGQFM-UHFFFAOYSA-N 0.000 claims description 2
- GBYFFQSMDBOMCX-UHFFFAOYSA-N 2-(dibromoamino)-5-phosphonopentanoic acid Chemical compound OC(=O)C(N(Br)Br)CCCP(O)(O)=O GBYFFQSMDBOMCX-UHFFFAOYSA-N 0.000 claims description 2
- IHEFYJCAHPMNNZ-UHFFFAOYSA-N 2-(dichloroamino)-8-phosphonooctanoic acid Chemical compound OC(=O)C(N(Cl)Cl)CCCCCCP(O)(O)=O IHEFYJCAHPMNNZ-UHFFFAOYSA-N 0.000 claims description 2
- CNZIVXGNLPHOKV-UHFFFAOYSA-N 2-(dichloroamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(Cl)Cl CNZIVXGNLPHOKV-UHFFFAOYSA-N 0.000 claims description 2
- KHPJMTPAUHAEEI-UHFFFAOYSA-N 2-(dichloroamino)ethylphosphonic acid Chemical compound OP(O)(=O)CCN(Cl)Cl KHPJMTPAUHAEEI-UHFFFAOYSA-N 0.000 claims description 2
- FWACYDHVHFBQHS-UHFFFAOYSA-N 2-(dichloroamino)propan-2-ylphosphonic acid Chemical compound ClN(Cl)C(C)(C)P(O)(O)=O FWACYDHVHFBQHS-UHFFFAOYSA-N 0.000 claims description 2
- WYRXPDKKQWTPKX-UHFFFAOYSA-N 2-(dichloroamino)propane-1-sulfonic acid Chemical compound ClN(Cl)C(C)CS(O)(=O)=O WYRXPDKKQWTPKX-UHFFFAOYSA-N 0.000 claims description 2
- LDSLVJUAHMPZBB-UHFFFAOYSA-N 2-(diiodoamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(I)I LDSLVJUAHMPZBB-UHFFFAOYSA-N 0.000 claims description 2
- XUGMGYUIGNYMJQ-UHFFFAOYSA-N 2-(iodoamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNI XUGMGYUIGNYMJQ-UHFFFAOYSA-N 0.000 claims description 2
- BCGSUNSECWTYNJ-UHFFFAOYSA-M 2-[3-(chloroamino)-3-methylbutyl]sulfonylethyl-trimethylazanium;chloride Chemical compound [Cl-].ClNC(C)(C)CCS(=O)(=O)CC[N+](C)(C)C BCGSUNSECWTYNJ-UHFFFAOYSA-M 0.000 claims description 2
- JWYOWSSRRLJTQF-UHFFFAOYSA-M 2-[3-(dichloroamino)-3-methylbutyl]sulfonylethyl-trimethylazanium;chloride Chemical compound [Cl-].ClN(Cl)C(C)(C)CCS(=O)(=O)CC[N+](C)(C)C JWYOWSSRRLJTQF-UHFFFAOYSA-M 0.000 claims description 2
- GDVDLFHXJBBZOE-UHFFFAOYSA-N 3-(chloroamino)-2,2,3-trimethylbutanoic acid Chemical compound ClNC(C)(C)C(C)(C)C(O)=O GDVDLFHXJBBZOE-UHFFFAOYSA-N 0.000 claims description 2
- OXIWSCWSIBBUDO-UHFFFAOYSA-N 3-(dichloroamino)-2,2,3-trimethylbutanoic acid Chemical compound ClN(Cl)C(C)(C)C(C)(C)C(O)=O OXIWSCWSIBBUDO-UHFFFAOYSA-N 0.000 claims description 2
- RRMNYNZNVLQUBK-UHFFFAOYSA-M 3-[3-(chloroamino)-3-methylbutyl]sulfonylpropyl-trimethylazanium;chloride Chemical compound [Cl-].ClNC(C)(C)CCS(=O)(=O)CCC[N+](C)(C)C RRMNYNZNVLQUBK-UHFFFAOYSA-M 0.000 claims description 2
- IDEHEMJHWQSEJL-UHFFFAOYSA-M 3-[3-(dichloroamino)-3-methylbutyl]sulfonylpropyl-trimethylazanium;chloride Chemical compound [Cl-].ClN(Cl)C(C)(C)CCS(=O)(=O)CCC[N+](C)(C)C IDEHEMJHWQSEJL-UHFFFAOYSA-M 0.000 claims description 2
- CEWZMYBSKUHYMS-UHFFFAOYSA-N 4-(chloroamino)-4-phosphonobutanoic acid Chemical compound OC(=O)CCC(NCl)P(O)(O)=O CEWZMYBSKUHYMS-UHFFFAOYSA-N 0.000 claims description 2
- DWYLYZGWBIVRGV-UHFFFAOYSA-N 4-(dichloroamino)-4-phosphonobutanoic acid Chemical compound OC(=O)CCC(N(Cl)Cl)P(O)(O)=O DWYLYZGWBIVRGV-UHFFFAOYSA-N 0.000 claims description 2
- GWIUGRDUEQIQFY-UHFFFAOYSA-M N,N-dichloro-2-methyl-1-(1-methylpiperidin-1-ium-1-yl)propan-2-amine;chloride Chemical compound [Cl-].ClN(Cl)C(C)(C)C[N+]1(C)CCCCC1 GWIUGRDUEQIQFY-UHFFFAOYSA-M 0.000 claims description 2
- SEHPLDLDSGWWRP-UHFFFAOYSA-M N-chloro-2-methyl-1-(1-methylpiperidin-1-ium-1-yl)propan-2-amine;chloride Chemical compound [Cl-].ClNC(C)(C)C[N+]1(C)CCCCC1 SEHPLDLDSGWWRP-UHFFFAOYSA-M 0.000 claims description 2
- YKTCVYHHAFHLHL-JEDNCBNOSA-N OBO.CC(C)C[C@H](N(Cl)Cl)C(O)=O Chemical compound OBO.CC(C)C[C@H](N(Cl)Cl)C(O)=O YKTCVYHHAFHLHL-JEDNCBNOSA-N 0.000 claims description 2
- DARKVQOMVNRQNZ-JEDNCBNOSA-N OBO.CC(C)C[C@H](NCl)C(O)=O Chemical compound OBO.CC(C)C[C@H](NCl)C(O)=O DARKVQOMVNRQNZ-JEDNCBNOSA-N 0.000 claims description 2
- DXDZUCBULNMIIX-UHFFFAOYSA-N OBO.OC(=O)CCN(Cl)Cl Chemical compound OBO.OC(=O)CCN(Cl)Cl DXDZUCBULNMIIX-UHFFFAOYSA-N 0.000 claims description 2
- KXCDENIMXRKIPT-UHFFFAOYSA-N OBO.OC(=O)CCNCl Chemical compound OBO.OC(=O)CCNCl KXCDENIMXRKIPT-UHFFFAOYSA-N 0.000 claims description 2
- GBUDGXDEROGHBY-JEDNCBNOSA-N OP(O)=O.CC(C)C[C@H](N(Cl)Cl)C(O)=O Chemical compound OP(O)=O.CC(C)C[C@H](N(Cl)Cl)C(O)=O GBUDGXDEROGHBY-JEDNCBNOSA-N 0.000 claims description 2
- LDCBEAIUZPYSBX-JEDNCBNOSA-N P(O)(O)=O.ClN[C@@H](CC(C)C)C(=O)O Chemical compound P(O)(O)=O.ClN[C@@H](CC(C)C)C(=O)O LDCBEAIUZPYSBX-JEDNCBNOSA-N 0.000 claims description 2
- NYSPQPYUHCFZRP-UHFFFAOYSA-N [1-(chloroamino)cyclohexyl]methanesulfonic acid Chemical compound OS(=O)(=O)CC1(NCl)CCCCC1 NYSPQPYUHCFZRP-UHFFFAOYSA-N 0.000 claims description 2
- UEQTVRUQHVQHSW-UHFFFAOYSA-N [1-(dichloroamino)-2-methylpropyl]phosphonic acid Chemical compound CC(C)C(N(Cl)Cl)P(O)(O)=O UEQTVRUQHVQHSW-UHFFFAOYSA-N 0.000 claims description 2
- XFNJJSSPIZPGBG-UHFFFAOYSA-N [1-(dichloroamino)cyclohexyl]methanesulfonic acid Chemical compound OS(=O)(=O)CC1(N(Cl)Cl)CCCCC1 XFNJJSSPIZPGBG-UHFFFAOYSA-N 0.000 claims description 2
- AVVXXYCPMYUMEO-UHFFFAOYSA-M [2-(chloroamino)-2-methylpropyl]-dimethylsulfanium;chloride Chemical compound [Cl-].C[S+](C)CC(C)(C)NCl AVVXXYCPMYUMEO-UHFFFAOYSA-M 0.000 claims description 2
- ZCOWIFNURMQKJU-UHFFFAOYSA-M [2-(dichloroamino)-2-methylpropyl]-dimethylsulfanium;chloride Chemical compound [Cl-].C[S+](C)CC(C)(C)N(Cl)Cl ZCOWIFNURMQKJU-UHFFFAOYSA-M 0.000 claims description 2
- ICVCXWDNNTUJIO-UHFFFAOYSA-M [4-(chloroamino)-4-methylpentyl]-trimethylphosphanium;chloride Chemical compound [Cl-].ClNC(C)(C)CCC[P+](C)(C)C ICVCXWDNNTUJIO-UHFFFAOYSA-M 0.000 claims description 2
- AXRFRMUBAWDOHG-UHFFFAOYSA-M [4-(dichloroamino)-4-methylpentyl]-trimethylphosphanium;chloride Chemical compound [Cl-].ClN(Cl)C(C)(C)CCC[P+](C)(C)C AXRFRMUBAWDOHG-UHFFFAOYSA-M 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 229940002612 prodrugs Drugs 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 201000004813 bronchopneumonia Diseases 0.000 claims 7
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 4
- 208000004361 Obstructive Lung Disease Diseases 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- 201000003883 cystic fibrosis Diseases 0.000 claims 2
- 201000009910 diseases by infectious agent Diseases 0.000 claims 2
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical group ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 150000007513 acids Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4379108P | 2008-04-10 | 2008-04-10 | |
| US61/043,791 | 2008-04-10 | ||
| PCT/US2009/040251 WO2009126912A1 (fr) | 2008-04-10 | 2009-04-10 | Compositions comprenant une amine n-halogénée ou n,n-dihalogénée pour le traitement et la prophylaxie des infections broncho-pulmonaires |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011516578A JP2011516578A (ja) | 2011-05-26 |
| JP2011516578A5 true JP2011516578A5 (fr) | 2012-06-07 |
Family
ID=40833504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011504210A Pending JP2011516578A (ja) | 2008-04-10 | 2009-04-10 | 気管支肺感染症の治療および予防のための組成物および方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20110151025A1 (fr) |
| EP (1) | EP2265267B1 (fr) |
| JP (1) | JP2011516578A (fr) |
| ES (1) | ES2608047T3 (fr) |
| WO (1) | WO2009126912A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2341886B1 (fr) * | 2008-11-07 | 2015-08-26 | NovaBay Pharmaceuticals, Inc. | Compositions antimicrobiennes n-chlorées |
| AU2011317223A1 (en) * | 2010-10-19 | 2013-05-23 | Novabay Pharmaceuticals, Inc. | Antimicrobial polyether and polyol compounds |
| EP3469117B1 (fr) | 2016-06-09 | 2022-01-26 | De Nora Holdings US, Inc. | Production électrolytique de solutions organiques de chloramine |
| US20220273594A1 (en) * | 2021-02-26 | 2022-09-01 | Markus Nagl | Compositions and Use of N-Chlorotaurine for Treatment and Prevention of Respiratory Infections |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950536A (en) | 1974-02-01 | 1976-04-13 | Sol Joseph Barer | N,N-Dichloro substituted aminocarboxylic acids as bactericides and fungicides |
| CA2320556A1 (fr) * | 1999-09-29 | 2001-03-29 | Queen's University At Kingston | N',n'-dichloro-omega-aminoacides et leurs derives et leurs utilisations |
| US20040116521A1 (en) * | 2000-09-14 | 2004-06-17 | Waldemar Gottardi | Fungicidal agent containing n-chlorotaurine and use thereof |
| FR2819723B1 (fr) * | 2001-01-23 | 2006-11-17 | Arnaud Mainnemare | Composition halogene, son procede de preparation et ses utilisations |
| PL1656095T3 (pl) | 2003-08-18 | 2014-04-30 | Novabay Pharmaceuticals Inc | N,n-dwuchlorowcowane kwasy aminowe i pochodne |
| TWI386201B (zh) * | 2005-01-25 | 2013-02-21 | Novabay Pharmaceuticals Inc | Ｎ-鹵化胺基酸、ｎ，ｎ-二鹵化胺基酸與其衍生物；以及使用其之組合物與方法 |
| WO2007044559A1 (fr) | 2005-10-06 | 2007-04-19 | Novabay Pharmaceuticals, Inc. | Systeme et methode de prevention des infections bacteriennes et fongiques y compris des infections des voies urinaires (uti) au moyen d'acides amines n-halogenes |
| TW200843787A (en) * | 2006-12-29 | 2008-11-16 | Novabay Pharmaceuticals Inc | N-halogenated amino compounds and derivatives; compositions and methods of using them |
| UY31057A1 (es) * | 2007-05-01 | 2008-10-31 | Alcon Res Ltd | Formulaciones de aminoacido n-halogenado que contiene acido alifatico |
| UY31059A1 (es) * | 2007-05-01 | 2008-10-31 | Alcon Res Ltd | Formulaciones de aminoacido n-halogenado |
| UY31058A1 (es) * | 2007-05-01 | 2008-10-31 | Alcon Res Ltd | Formulaciones de aminoacido n-halogenado con compuestos antiinflamatorios |
-
2009
- 2009-04-10 ES ES09729990.3T patent/ES2608047T3/es active Active
- 2009-04-10 JP JP2011504210A patent/JP2011516578A/ja active Pending
- 2009-04-10 WO PCT/US2009/040251 patent/WO2009126912A1/fr active Application Filing
- 2009-04-10 EP EP09729990.3A patent/EP2265267B1/fr active Active
- 2009-04-10 US US12/936,508 patent/US20110151025A1/en not_active Abandoned
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